US3043785A - Depigmenting polymeric compositions with aliphatic carboxylic acid settling aids - Google Patents

Depigmenting polymeric compositions with aliphatic carboxylic acid settling aids Download PDF

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US3043785A
US3043785A US74859258A US3043785A US 3043785 A US3043785 A US 3043785A US 74859258 A US74859258 A US 74859258A US 3043785 A US3043785 A US 3043785A
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pigment
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aqueous phase
solution
polymer
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Palmer W Wright
Bernie A Kozakiewicz
Arthur F Roche
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Dow Chemical Co
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00Recovery or working-up of waste materials
    • C08J11/04Recovery or working-up of waste materials of polymers
    • C08J11/06Recovery or working-up of waste materials of polymers without chemical reactions
    • C08J11/08Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02WCLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00Technologies for solid waste management
    • Y02W30/50Reuse, recycling or recovery technologies
    • Y02W30/62Plastics recycling; Rubber recycling

Definitions

  • pigment polymer compositions for coloration, delustering and various other purposes.
  • inorganic pigments for example, are cadium and selenium compounds, titania, the several chromium oxides and the like.
  • pigmented polymeric compositions may advantageously be depigmented by practice of a method in accordance with the method of the present invention which comprises dissolving a pigmented polymeric composition that is desired to be reclaimed in a suitable non-reactive, water-insoluble, organic solvent that beneficially, if possi ible, may be a hydrocarbon or closely-related solvent; intimately mixing the resulting organic solution containing the dispersed pigment with an aqueous phase that is adapted to accelerate pigment settling and which contains dissolved therein a Water-soluble chemical settling aid that is non-reactive with the polymer and which is a watersoluble aliphatic carboxylic (including polycarboxylic) acid that contains no more than (and, preferably, no more than 3) carbon atoms in its molecule; and then separating the organic polymer solution from the pigment and the aqueous phase, advantageously by settling the organic polymer solution from the aqueous phase; separating the organic polymeric solution from the aqueous phase; filter
  • decantation of the organic polymer solution in order to separate it fromthe aqueous phase after the mixing and settling of the two is made much easier and appreciably more eificient. It also facilitates complete isolation of the polymer solution by filtration or centrifugation procedures for pigment separation, when performed either prior to or after the separation of the liquid phases.
  • thermoplastic polymeric material can be reclaimed from scrap or other pigmented compositions by the procedure of the present invention.
  • polyester such as polyethylene terephthalate and the like
  • acrylonitrile polymer including polyacrylonitrile the carbon atoms in alkyl substituents
  • the aromatic portion of the compound as styrene the several chlorostyrenes, the several methyl styrenes (including vinyl toluene), the several ethyl styrenes, vinyl naphthalene and the like as well as the solid resinous copolymers of such compounds with one another and with other unsaturated monomeric materials including acrylonitrile, methyl methacryla-te, ethyl acrylate, a-methyl styrene and other monoethylenically unsaturated monomers and divinyl benzene, diallyl maleate and the like.
  • any non-reactive, water-insoluble, organic solvent liquid may be employed in the practice of the invention for dissolving the scrap polymer composition that is to be depigrnented and reclaimed.
  • the particular solvent that is used depends on the particular polymer that is involved.
  • styrene polymers including polystyrene, it is generally suitable to employ ethyl benzene, xylene, toluene, and the like or an equivalent Water-insoluble aromatic hydrocarbon solvent among the known water-insoluble for such polymers.
  • the amount of the settling aid that may be incorporated in the aqueous phase with which the dissolved polymer solution is treated may be found to vary over a wide range. depending upon the characteristics of the t particular settling agent that is utilized when one is being employed and upon the nature and quantity of the pigment that is beingrremoved from the polymer composition .being reclaimed. It is ordinarily beneficial when it is possible to doso for the aqueous phase to contain between about 0.5 and 50 percent by, weight based on the weight of thepaqueous solution of the chemical settling aid that .is employed. It is generally more practical for the aqueous phase to contain at least about percent by weight .of the chemical settling aid.
  • the precise amount of the-settling aid that-is employed may, of course, vary with the particular characteristics of the material and the aqueous phase for each treatment of the organic ,polymflr solution that is about one-half to fifty times by the polymer composition. 7 In many cases it may be suitable and preferred for an amount of settling aid to be employed that isnot more than twenty times the weight of the pigment.
  • the relative quantity of the organic polymer solution and the aqueous treating phase may also vary over wide ranges. As little, for example, .as about 1 to as much .a sfabout 9 parts 'by weight or more of aqueous phase for. each part, by weight of polymeric solution that is being "treated may be satisfactorily employed. It is generally preferred for the weight ratio of the organic polymer solution to the aqueous treating phase to be about two or three to one, respectively.
  • Typical of the'aliphatic vcarboxylic acid settling aids that may be utilized are acetic acid, propionic acid and oxalicl acid.
  • the depigmented polymer solution may be isolated and separated from the settled pigment by filtering or centrifuging it prior to the phase separation of the immiscible liquids, or subsequent thereto if the settling of the pigment out of the organic phase has not gone to completion before their separation upon stratification.
  • Example I About three parts of asaturated aqueous solution (containing less than about 50 percent) of oxalic acid in dis.- tilled water was added to about seven parts of a solution containing about 10 percent of polystyrene pigmented with about 2 percent by weight of titanium dioxide, in toluene. The two phases were shakentogethcr and intimately intermixed for about 10 minutes at a temperature of 80 to 85- C. after which they were allowed to settle. The depigmented organic polymeric solution was then decanted and subjected to a spectrophotometric light yweight theweight .of the pigment. being removed from 7 have settled out.
  • the polystyrene (which was'reclaimed 'by vacuum devolatilization of the solvent vehicle for 2 7 ,hours at 4, mm. Hg and 150 C.) had properties-and tion of the pigment.' These include such material as cellulose, hydroxypropyl methyl cellulose and the like which may be employed in viscosity grades between about .10 and 2,000, preferably about five hundred, centipoises as determined by measurement of their two percent aqueous solutionsnat room temperature.
  • the intimate mixture of the phases during the actual depigrnentation interval may be accomplished by any conventional mixing or physical agitating technique using ordinary apparatus for such purpose.
  • atroom I temperatures each. treatment may beaccomplished within an hour beforeseparafing the phases.
  • elevated temperatures. areemployed during the intermixing of the phases, shorter periods of time'(as, for example, 10 minutes or less) maybe foundto sufiice.
  • the organic polymeric solution may be separated from V the usually heavier aqueous phaserin any desired manner other. separatory techniques. After the dissolved polymer has'been filtereisubsequent to its depigmentation, .it may be isolated in any desired manner, including solvent Color about asgood as virgin polymer styrene.
  • Example II The procedure of Example 1 is repeated with about 28 parts. of the same organic polymer solutionland 12 parts .of an aqueous phase, excepting that the aqueous phase .consists o f a 40 percent aqueous solution of acetic acid. After shaking and settling ,in the same way, the depigmented organic solution is v,found .to havea 3 per.- .cent light transmission reading, corresponding -to-that ob.- tained in a standard solution .in' which -90 percent of the pigment .hasbeen settled out.
  • Example III cellulose, having a viscosity rating of about 500 centitheindi cated varieties .are employed-fertile depigmenta poises, in each of the aqueous phases.
  • Quantities of the ,cellulose ether .as low as 0.1 percent .by- ,weight also provide highly satisfactory facilitation .ofthe fiocculationof the settled pigment;
  • Method for depigmenting synthetic, thermoplastic polymeric compositions which comprises dissolving a pigmented polymeric composition containing an inorganic pigment that is insoluble in solvents in which said polymeric composition is dissolved in a water-insoluble organic solvent for said polymeric composition that is non-reactive with said polymer and said pigments and in which said pigment is insoluble; intimately mixing each part by weight of the resulting organic solution containing the dispersed pigment with between about 1 and 9 parts by weight of an aqueous phase that contains dissolved therein between about 0.5 and 50 weight percent, based on the weight of the aqueous phase, of a watersoluble aliphatic carboxylic acid that contains not more than about 5 carbon atoms in its molecule; and then physically separating the organic polymeric solution'from the settled pigment and the aqueous phase.
  • the method 01 claim 1, wherein the organic polymeric solution and the aqueous phase are intermixed at an elevated, non-boiling temperature.

Description

atent 3,943,785 Patented July 10, 1%62 dice 3,043,785 DEPIGMENTING POLYMERIC COMPOSITIONS WITH ALIPHATIC CARBOXYLIC ACID SET- TLING AlDS Palmer W. Wright, Midland, Bernie A. Kozakiewicz, Bay City, and Arthur F. Roche, Freeland, Mich, assignors to The Dow Chemical Company, Midland, Mich., a corporation of Delaware No Drawing. Filed July 15, 1958, Ser. No. 748,592 13 Claims. (Cl. 260-23) This invention relates to an improved method for depigmenting polymeric compositions in order to reclaim the polymeric constituent therefrom for subsequent reuse in placeof or in combination with virgin polymer stock.
It is a common practice to pigment polymer compositions for coloration, delustering and various other purposes. Among the'more popular inorganic pigments, for example, are cadium and selenium compounds, titania, the several chromium oxides and the like. In order to reclaim and recover the polymer constituent from pigmented polymeric compositions, it is usually necessary to dissolve the composition in a suitable solvent therefor and to filter the resulting solution free from the insoluble pigment contained therein. This may oftentimes be a difiicult and tedious process and one that may frequently be rendered even more painstaking by the impossibility of rapidly filtering the solution, due to the tendency of many pigments to remain suspended in and to settle very slowly from the solution that is made of the pigmented polymeric composition (usually scrap material) being reclaimed.
It is the principal object of the present invention to provide an improved method for depigmenting polymer compositions to facilitate the easier and more economically attractive reclamation and recovery of the polymer constituent thereof. Other objects, advantages and benefits of the invention will be manifest in the ensuing description and specification.
To this end, pigmented polymeric compositions may advantageously be depigmented by practice of a method in accordance with the method of the present invention which comprises dissolving a pigmented polymeric composition that is desired to be reclaimed in a suitable non-reactive, water-insoluble, organic solvent that beneficially, if possi ible, may be a hydrocarbon or closely-related solvent; intimately mixing the resulting organic solution containing the dispersed pigment with an aqueous phase that is adapted to accelerate pigment settling and which contains dissolved therein a Water-soluble chemical settling aid that is non-reactive with the polymer and which is a watersoluble aliphatic carboxylic (including polycarboxylic) acid that contains no more than (and, preferably, no more than 3) carbon atoms in its molecule; and then separating the organic polymer solution from the pigment and the aqueous phase, advantageously by settling the organic polymer solution from the aqueous phase; separating the organic polymeric solution from the aqueous phase; filtering the separated polymeric solution; and subsequently isolating and recovering the reclaimed and depigmented polymer.
In many cases it is extremely advantageous to incorporate a minor proportion of a Water-soluble cellulose ether derivative, such as methyl cellulose and the like, in the aqueous phase before its intimate mixture with the organic polymer solution. This facilitates flocculation of the pigment in such a manner that the major proportion of the precipitate settles out in a clean and direct manner, as at'the liquid interface or'on thebottom of the container in which the depigrnentation is being conducted (when sedimentation techniques are being used for separation), without tending to accumulate on the sidewalls of the container or at any other point outside of that substantially encompassed by the stratified aqueous phase layer. By such means, decantation of the organic polymer solution in order to separate it fromthe aqueous phase after the mixing and settling of the two is made much easier and appreciably more eificient. It also facilitates complete isolation of the polymer solution by filtration or centrifugation procedures for pigment separation, when performed either prior to or after the separation of the liquid phases.
Practice of the method of the present invention conveniently permits the effective and efficient depigmentation and reclamation of scrap polymer. The reclaimed product -is generally obtained in a condition of purity and freedom from contamination by pigment materials that is equivalent to that of virgin stock with the desired result being achieved with utmost expedience and minimized operational difiiculty.
Any synthetic, thermoplastic polymeric material can be reclaimed from scrap or other pigmented compositions by the procedure of the present invention.
polyester (such as polyethylene terephthalate and the like), acrylonitrile polymer (including polyacrylonitrile the carbon atoms in alkyl substituents) in the aromatic portion of the compound as styrene, the several chlorostyrenes, the several methyl styrenes (including vinyl toluene), the several ethyl styrenes, vinyl naphthalene and the like as well as the solid resinous copolymers of such compounds with one another and with other unsaturated monomeric materials including acrylonitrile, methyl methacryla-te, ethyl acrylate, a-methyl styrene and other monoethylenically unsaturated monomers and divinyl benzene, diallyl maleate and the like.
Any non-reactive, water-insoluble, organic solvent liquid may be employed in the practice of the invention for dissolving the scrap polymer composition that is to be depigrnented and reclaimed. Obviously, the particular solvent that is used depends on the particular polymer that is involved. For styrene polymers, including polystyrene, it is generally suitable to employ ethyl benzene, xylene, toluene, and the like or an equivalent Water-insoluble aromatic hydrocarbon solvent among the known water-insoluble for such polymers. When certain copolymeric styrene polymers, such as copolymers of styrene and acrylonitrile, are involved, it may sometimesbe preferable to employ relatively more polar solvents, such as methyl ethyl ketone and the like,.for their dissolution. Although it is preferred, as a matter of expedience, to utilize a solvent that is practically effective at normal room temperatures and under normal atmospheric pressure, it is possible to accomplish the dissolution and it is generally advantageousto conduct themethod of the invention at elevated temperatures. It is also possible to employ superatmospheric pressures in combination with an elevated dissolving and treating temperature. In most cases, however, it may be found better to avoid greater For example, various polyamide (such as nylon 66 and nylon 6),
necessary volumes of the desired polymer in solution while permitting a suitable settling efiect to be accomplished during the ,depigmentation process. 7
The amount of the settling aid that may be incorporated in the aqueous phase with which the dissolved polymer solution is treated may be found to vary over a wide range. depending upon the characteristics of the t particular settling agent that is utilized when one is being employed and upon the nature and quantity of the pigment that is beingrremoved from the polymer composition .being reclaimed. It is ordinarily beneficial when it is possible to doso for the aqueous phase to contain between about 0.5 and 50 percent by, weight based on the weight of thepaqueous solution of the chemical settling aid that .is employed. It is generally more practical for the aqueous phase to contain at least about percent by weight .of the chemical settling aid. The precise amount of the-settling aid that-is employed may, of course, vary with the particular characteristics of the material and the aqueous phase for each treatment of the organic ,polymflr solution that is about one-half to fifty times by the polymer composition. 7 In many cases it may be suitable and preferred for an amount of settling aid to be employed that isnot more than twenty times the weight of the pigment. The relative quantity of the organic polymer solution and the aqueous treating phase may also vary over wide ranges. As little, for example, .as about 1 to as much .a sfabout 9 parts 'by weight or more of aqueous phase for. each part, by weight of polymeric solution that is being "treated may be satisfactorily employed. It is generally preferred for the weight ratio of the organic polymer solution to the aqueous treating phase to be about two or three to one, respectively.
Typical of the'aliphatic vcarboxylic acid settling aids that may be utilized :are acetic acid, propionic acid and oxalicl acid.
:lBcsides'methyl celluloseQother water-soluble cellulose .etherderivatives may also be incorporated with advantage in'theaqueous phasejn order to obtain better precipitathe volume of water-that is actually used in the aqueous 4 f stripping, precipitation in a liquid vehicle followed by filtration and the like.
Alternatively, as has been, indicated, the depigmented polymer solution may be isolated and separated from the settled pigment by filtering or centrifuging it prior to the phase separation of the immiscible liquids, or subsequent thereto if the settling of the pigment out of the organic phase has not gone to completion before their separation upon stratification. Y I
The invention is further illustrated in and by the following examples, wherein unless otherwise indicated, all parts and percentages are to be taken by Weight.
Example I About three parts of asaturated aqueous solution (containing less than about 50 percent) of oxalic acid in dis.- tilled water was added to about seven parts of a solution containing about 10 percent of polystyrene pigmented with about 2 percent by weight of titanium dioxide, in toluene. The two phases were shakentogethcr and intimately intermixed for about 10 minutes at a temperature of 80 to 85- C. after which they were allowed to settle. The depigmented organic polymeric solution was then decanted and subjected to a spectrophotometric light yweight theweight .of the pigment. being removed from 7 have settled out.
transmission test,,using a model B .Beckman spectrophotometer Withlight having a wave length of about 550 an, measured through a cell in which the solution .was contained having a thickness .of about 11 centimeter. After about 15 minutes settling, ,a 3 percent transmission read ing was obtained' This corresponded to the reading that was obtained with a standard solution of thesame type in which 90 percent of the pigment had been knownto In comparison, the same solution of the pigmented polymer in toluene (without having'been treated as above) wasfound, after 15' minutes settling, to have 0 Percent light transmission.
Upon recovery of the polymer from the organic-solution that had been depigmented -with the aqueous solution of oxalic acid, the polystyrene (which was'reclaimed 'by vacuum devolatilization of the solvent vehicle for 2 7 ,hours at 4, mm. Hg and 150 C.) had properties-and tion of the pigment.' These include such material as cellulose, hydroxypropyl methyl cellulose and the like which may be employed in viscosity grades between about .10 and 2,000, preferably about five hundred, centipoises as determined by measurement of their two percent aqueous solutionsnat room temperature. It 'is ordinarily satisfactory to .employ between about 0.10 and '1 percent by weight of the cellulose ether derivative in the aqueous phase, based on the Weight of the aqueous solution. It is usually advantageous to employ between about 0.10 and 0.25 percentby weight of the cellulose derivative;
The intimate mixture of the phases during the actual depigrnentation interval may be accomplished by any conventional mixing or physical agitating technique using ordinary apparatus for such purpose. Usually, atroom I temperatures, each. treatment may beaccomplished within an hour beforeseparafing the phases. When elevated temperatures. areemployed during the intermixing of the phases, shorter periods of time'(as, for example, 10 minutes or less) maybe foundto sufiice. Aftersettling, the organic polymeric solution may be separated from V the usually heavier aqueous phaserin any desired manner other. separatory techniques. After the dissolved polymer has'been filtereisubsequent to its depigmentation, .it may be isolated in any desired manner, including solvent Color about asgood as virgin polymer styrene.
Example II The procedure of Example 1 is repeated with about 28 parts. of the same organic polymer solutionland 12 parts .of an aqueous phase, excepting that the aqueous phase .consists o f a 40 percent aqueous solution of acetic acid. After shaking and settling ,in the same way, the depigmented organic solution is v,found .to havea 3 per.- .cent light transmission reading, corresponding -to-that ob.- tained in a standard solution .in' which -90 percent of the pigment .hasbeen settled out.
Example III ,cellulose, having a viscosity rating of about 500 centitheindi cated varieties .are employed-fertile depigmenta poises, in each of the aqueous phases. The ,fiocksof pigment .which are .formeddep'os it directly at the interface between the aqueous and the organic solutions without accumulating or depositing on the side wall of the vessel. Quantities of the ,cellulose ether .as low as 0.1 percent .by- ,weight also provide highly satisfactory facilitation .ofthe fiocculationof the settled pigment;
Similar excellent resultsmay be ,obtained when other waterrsoluble aliphatic ,,carboxylic acid settling aids Tot tion and other materialsare removed frorn othenpplystyrene and analogous polymer compositions-of the varieties mentioned. i j I v The scope. andpurviewofthe present invention is to be gauged in the light of the;her eto appendedclairns rather than strictly from the foregoing illustrative description and specification. v
What is claimed is:
1. Method for depigmenting synthetic, thermoplastic polymeric compositions which comprises dissolving a pigmented polymeric composition containing an inorganic pigment that is insoluble in solvents in which said polymeric composition is dissolved in a water-insoluble organic solvent for said polymeric composition that is non-reactive with said polymer and said pigments and in which said pigment is insoluble; intimately mixing each part by weight of the resulting organic solution containing the dispersed pigment with between about 1 and 9 parts by weight of an aqueous phase that contains dissolved therein between about 0.5 and 50 weight percent, based on the weight of the aqueous phase, of a watersoluble aliphatic carboxylic acid that contains not more than about 5 carbon atoms in its molecule; and then physically separating the organic polymeric solution'from the settled pigment and the aqueous phase.
2. The method of claim 1 and including the additional step of dissolving between about 0.1 and 1.0 percent by weight of a water-soluble cellulose ether derivative in said aqueous phase.
3. The method of claim 2, wherein between about 0.1 and 0.25 percent by weight of the cellulose ether is dissolved in said aqueous phase.
4. The method of claim 2, wherein the cellulose ether derivative is methyl cellulose.
5. The method of claim 1, wherein said water-soluble, aliphatic carboxylic acid is oxalic acid.
6. The method of claim 1, wherein said water-soluble, aliphatic carboxylic acid is acetic acid.
7. The method of claim 1, wherein the quantity of 6 settling aid that is added to said solution is an amount that is from about one-half to fifty times by weight the quantity of pigment being removed from the polymeric composition.
8. The method of claim 1, wherein the organic polymer solution contains at least about 5 percent by weight based on the weight of the solution, of the polymeric composition that is to be depigmented.
9. The method of claim 1, wherein between about 10 and 35 percent by weight of the aqueous phase is employed for treating the polymeric solution that is being depigmented, based on the total weight of the aqueous phase and the organic polymer solution.
10. The method of claim 1, wherein the polymer is a vinyl aromatic polymer.
11. The method of claim 1, wherein the polymer is polystyrene and the solvent is ethylbenzene.
12. The method of claim. 1, wherein the polymer is polystyrene and the solvent is toluene.
13. The method 01 claim 1, wherein the organic polymeric solution and the aqueous phase are intermixed at an elevated, non-boiling temperature.
References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. METHOD FOR DEPIGMENTING SYNTHETIC, THERMOPLASTIC POLYMERIC COMPOSITIONS WHICH COMPRISES DISSOLVING A PIGMENTED POLYMERIC COMPOSITION COSNTAINING AN INORGANIC PIGMENT THAT IS INSOLUBLE IN SOLVENTS IN WHICH SAID POLYMERIC COMPOSITION IS DISSOLVED IN A WATER-INSOLUBLE ORGANIC SOLVENT FOR SAID POLYMERIC COMPOSITION THAT IS NON-REACTIVE WITH SAID POLYMER AND SAID PIGMENTS AND IN WHICH SAID PIGMENT IS SOLUBLE; INTIMATELY MIXING EACH PART BY WEIGHT OF THE RESULTING ORGANIC SOLUTION CONTAINING THAE DISPERSED PIGMENT WITH BETWEEN ABOUT 1 AND 9 PARTS BY WEIGHT OF AN AQUEOUS PHASE THAT CONTAINS DISSOLVED THEREIN BETWEEN ABOUT 0.5 AND 50 WEIGHT PERCENT. BASED ON THE WEIGHT OF THE AQUEOUS PHASE, OF A WATERSOLUBLE ALIPHATIC CARBOXYLIC ACID THAT CONTAINS NOT MORE THAN ABOUT 5 CARBON ATOMS IN ITS MOLECULE; AND THEN PHYSICALLY SEPARATING THE ORGANIC POLYMERIC SOLUTION FROM THE SETTLED PIGMENT AND THE AQUEOUS PHASE.
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3226343A (en) * 1962-04-26 1965-12-28 Champion Papers Inc Process of recovery of polyethylene from cellulosic fibers
US3232891A (en) * 1961-11-03 1966-02-01 Union Carbide Canada Ltd Process for removing carbon black from polyethylene
US4038219A (en) * 1976-03-25 1977-07-26 Western Electric Company, Inc. Reclamation processing of polyvinyl chloride-scrap materials and products produced thereby
US4071479A (en) * 1976-03-25 1978-01-31 Western Electric Company, Inc. Reclamation processing of vinyl chloride polymer containing materials and products produced thereby
US4137393A (en) * 1977-04-07 1979-01-30 Monsanto Company Polyester polymer recovery from dyed polyester fibers
FR2435289A1 (en) * 1978-09-07 1980-04-04 Nippon Paint Co Ltd PROCESS FOR THE RECOVERY OF THE RESINOUS COMPONENT FROM THE EXCESS OF A POWDER COATING COMPOSITION
US4543364A (en) * 1984-12-13 1985-09-24 The Dow Chemical Company Recovery of polyethylene terephthalate (PET)
WO1992007025A1 (en) * 1990-10-22 1992-04-30 Mobil Oil Corporation Decontamination of polystyrene
EP0509358A1 (en) * 1991-04-19 1992-10-21 Bayer Ag Process for removal of inorganic pigments from thermoplastic polycondensates
US6036726A (en) * 1995-10-27 2000-03-14 Solutia Inc. Process for separating polyamide from colorant
US20040082672A1 (en) * 2002-10-16 2004-04-29 Fuquan Zeng Process for recyling colored thermoplastic molded articles

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US2293514A (en) * 1940-09-06 1942-08-18 Hercules Powder Co Ltd Treatiment of oleoresin with oxalic acid
US2639278A (en) * 1950-12-22 1953-05-19 Polymer Corp Method of preparing finely divided nylon powder
US2728725A (en) * 1951-03-30 1955-12-27 Hercules Powder Co Ltd Water clarification using watersoluble cellulose derivative coagulation aid
US2744029A (en) * 1952-05-24 1956-05-01 Nat Lead Co Preparation of water dispersible titanium dioxide pigment
US2914492A (en) * 1957-04-05 1959-11-24 Dow Chemical Co Depigmenting alkenyl aromatic polymer compositions by the combined pigmentsettling action of an aliphatic carboxylic acid and a diatomaceous filter aid
US2915482A (en) * 1957-04-05 1959-12-01 Dow Chemical Co Depigmenting polymeric compositions with amine settling aids

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2293514A (en) * 1940-09-06 1942-08-18 Hercules Powder Co Ltd Treatiment of oleoresin with oxalic acid
US2639278A (en) * 1950-12-22 1953-05-19 Polymer Corp Method of preparing finely divided nylon powder
US2728725A (en) * 1951-03-30 1955-12-27 Hercules Powder Co Ltd Water clarification using watersoluble cellulose derivative coagulation aid
US2744029A (en) * 1952-05-24 1956-05-01 Nat Lead Co Preparation of water dispersible titanium dioxide pigment
US2914492A (en) * 1957-04-05 1959-11-24 Dow Chemical Co Depigmenting alkenyl aromatic polymer compositions by the combined pigmentsettling action of an aliphatic carboxylic acid and a diatomaceous filter aid
US2915482A (en) * 1957-04-05 1959-12-01 Dow Chemical Co Depigmenting polymeric compositions with amine settling aids

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232891A (en) * 1961-11-03 1966-02-01 Union Carbide Canada Ltd Process for removing carbon black from polyethylene
US3226343A (en) * 1962-04-26 1965-12-28 Champion Papers Inc Process of recovery of polyethylene from cellulosic fibers
US4038219A (en) * 1976-03-25 1977-07-26 Western Electric Company, Inc. Reclamation processing of polyvinyl chloride-scrap materials and products produced thereby
US4071479A (en) * 1976-03-25 1978-01-31 Western Electric Company, Inc. Reclamation processing of vinyl chloride polymer containing materials and products produced thereby
US4137393A (en) * 1977-04-07 1979-01-30 Monsanto Company Polyester polymer recovery from dyed polyester fibers
FR2435289A1 (en) * 1978-09-07 1980-04-04 Nippon Paint Co Ltd PROCESS FOR THE RECOVERY OF THE RESINOUS COMPONENT FROM THE EXCESS OF A POWDER COATING COMPOSITION
US4543364A (en) * 1984-12-13 1985-09-24 The Dow Chemical Company Recovery of polyethylene terephthalate (PET)
WO1992007025A1 (en) * 1990-10-22 1992-04-30 Mobil Oil Corporation Decontamination of polystyrene
EP0509358A1 (en) * 1991-04-19 1992-10-21 Bayer Ag Process for removal of inorganic pigments from thermoplastic polycondensates
US6036726A (en) * 1995-10-27 2000-03-14 Solutia Inc. Process for separating polyamide from colorant
US20040082672A1 (en) * 2002-10-16 2004-04-29 Fuquan Zeng Process for recyling colored thermoplastic molded articles

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